I want to pick up this par of Red Wing 1909 for casual and light winter wear. I've never really own this type of boots before. The closest thing I have to them is a pair of CT chelsea boots. What do you think?

1) the frye engineer boots--they are less "" than the harnesses
2) frye brando engineers and lace ups--great look, very, very nice. i like these the most!
3) alden indy's--great looking boot. goes great with selvage denim.

You might like these chelseas with rubber composite soles. These are my favorite boots. Great with jeans. Not as "rock-n-roll" as the engineers or bikers. More of an "Australian rancher" RM Williams Yard boot. Edit: I just noticed Skaglore also recommended these, too. Good taste, mate.

DarkNWorn - I just picked up a pair on eBay for around $120. They are factory seconds and have two very slight color variations in the leather. But, it actually looks like what light wear would look like, so no big deal.

First impressions: they are very stiff leather and the soles are mega-stiff. As work boots should be, they look and feel like they could take a beating for many years.

I've worn them sparingly for a few days and they're starting to loosen up.

Oh, one thing. I wear a 9 in almost everything. I bought a 9D and they're pretty large (mostly in length). I picked up a pair of the Redwing custom fit insoles (the ones you put in the oven to mold to your foot) and now they fit perfectly. They come with no insole to speak of, so you'll probably need something even if it's thin.

They aren't the most elegant for street boots, but they are exactly what I wanted. That said, I wouldn't have paid $300 for them.

Those cost over twice as much as the CT chelseas, and honestly, I find the Taunton last shape to be utterly hideous. I think the best way to go is to buy the CT chelseas for 150 and just have them immediately resoled in rubber for 60. 210 is still not a bad deal.